WO1981002022A1 - Provisional crown-and-bridge resin - Google Patents

Provisional crown-and-bridge resin Download PDF

Info

Publication number
WO1981002022A1
WO1981002022A1 PCT/US1981/000030 US8100030W WO8102022A1 WO 1981002022 A1 WO1981002022 A1 WO 1981002022A1 US 8100030 W US8100030 W US 8100030W WO 8102022 A1 WO8102022 A1 WO 8102022A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
powder
consisting essentially
ethyl methacrylate
weight
Prior art date
Application number
PCT/US1981/000030
Other languages
English (en)
French (fr)
Inventor
R Ibsen
W Glace
Original Assignee
R Ibsen
W Glace
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22339858&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1981002022(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by R Ibsen, W Glace filed Critical R Ibsen
Priority to BR8105861A priority Critical patent/BR8105861A/pt
Priority to AU67827/81A priority patent/AU539337B2/en
Publication of WO1981002022A1 publication Critical patent/WO1981002022A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/92—Polymers useful for replacing hard animal tissues, e.g. dentures, bones

Definitions

  • This invention relates to a provisional crown-and- bridge resin comprising a powder-liquid restorative system.
  • Provisional crown-and-bridge resins are used in the mouth after a dentist has prepared the tooth, as a short- term filling-like structure for the patient to use during the time the laboratory is manufacturing the permanent crown or other prosthesis. Typically these resins are supposed to remain in place for several weeks, but may, in some cases, remain for as long as two years or more.
  • the present invention provides a provisional or temporary crown-and-bridge resin based, in most instances, upon an ethyl methacrylate resin and a poly (ethyl methacrylate) powder.
  • the material has been made radio- paque by adding barium glass to the poly (ethyl methacrylate) powder.
  • the resin usually based on ethyl methacrylate monomer, has a high percentage of tetrahydrofurfuryl methacrylate.
  • the tetrahydrofurfuryl methacrylate is the sole resin component, except for some minor ingredients, such as anti-oxident, accelerator, etc.
  • the resin also may contain ethoxylated bisphenol A dimethacrylate as a major component.
  • the material is easy to handle. It sets into a putty or rubbery stage about 60 seconds to 2 1/2 minutes after activation and sets hard in about 3 1/2 to 6 minutes.
  • the invention comprises a liquid or resin and a powder which are mixed in proper proportions, typically in a ratio of about two parts of liquid to seven parts of powder, but this ratio may vary from about two to five parts of powder per part of liquid.
  • composition of the liquid resin lies within the following ranges: LIQUID RESIN
  • the powder is mixed with the liquid to achieve a thick but still favorable consistency, in an amount by weight of two to five parts of powder per part of liquid, typically in the ratio of seven parts of powder to two parts of liquid.
  • the powder may be varied by adding suitable color materials, suitable dyes or pigments so as to match the color of the teeth, especially when used for a portion of a tooth that is to be at the front of the mouth and exposed to viewers. Suitable materials include brown and yellow. dyes, titanium dioxide, cadmium sulfide, and black iron oxide, all used in small amounts.
  • Tetrahydrofurfuryl methacrylate 40 Ethyl methacrylate 60 2-hydroxy ⁇ thyl-p-toluidine 0. .5 Powder:
  • Powder Same as Example 13. Powder-to-R.esin ratio 3.5:1.0 Liquid Resin Cure Characteristics Example Ratio of A:B Stringy Rubbery Hard 15 1/9 200 sec 220 sec 16 2/8 200 230 17 3/7 170 185 18 4/6 80 180 210 19 5/5 80 175 255 20 6/4 80 135 265 21 7/3 55 100 273 22 8/2 70 100 280 23 9/1 60 135 345 EXAMPLE 24
  • the benzoyl peroxide can be used at quantities from about 0.1% to about 5%. As the tertiary amine content decreases, the peroxide should increase.
  • the butylated hydroxytoluene can be used in amounts from about 0.01 to about 1.0%.
  • Other usable antioxidents include:
  • Methyl ether of hydroquinone at about 0.1 to about 5%.
  • N,N-dimethyl-p-toluidine at about 1/4-1/2 concentration of 2-HEPT.
  • the material has been found to be non-irritative to the gingival tissue, which is very important, and it has excellent stability with virtually no shrinkage on curing, as will be shown below. This enables it to remain in place for periods of even longer duration than are ordinarily expected for the laboratory to make the prosthesis. Its hardness is quite satisfactory. Its toughness enables it to be used for its purpose with very satisfactory results, although it can easily be removed in the same manner as other previously used materials. The fact that it is X-ray. opaque means that it not only can be detected by X-ray but also that it will look normal in the mouth when its appearance must be relied upon. Cure Shrinkage
  • a quick and reproduceable measurement of cure- shrinkage of polymeric dental restorative materials may be made with the aid of a quartz-tube dilatometer, such as that manufactured by Tinius-Olsen of Willow Grave, Pa.
  • the device comprises a quartz tube into which a quartz rod is fitted.
  • a fixture attached to the quartz tube enables positioning and locking of a dial indicator gage.
  • a sample is placed into the bottom of the quartz tube, the quartz rod is placed atop the sample, and the dial gage is positioned to a mid-scale reading and locked. Any changes in sample length are recorded with an accuracy of 0.001 mm.
  • 3-ml. glass syringes manufactured by MPL Corporation, Chicago IL. These syringes have a silicone-coated glass barrel, two end fixtures of polyethylene, and a silicone rubber plunger. The syringes were modified by removing the plunger and twisting off the rear polyethylene closure.
  • Enough material was mixed to fill a syringe to a depth of approximately 10 mm. In practice, some trial and error may be required to determine the correct amount.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)
  • Stringed Musical Instruments (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Golf Clubs (AREA)
  • Materials For Medical Uses (AREA)
  • Multicomponent Fibers (AREA)
  • Investigating Or Analyzing Materials By The Use Of Ultrasonic Waves (AREA)
PCT/US1981/000030 1980-01-14 1981-01-02 Provisional crown-and-bridge resin WO1981002022A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
BR8105861A BR8105861A (pt) 1980-01-14 1981-01-02 Resina para coroa e ponte provisorias
AU67827/81A AU539337B2 (en) 1980-01-14 1981-01-02 Provisional crown-and-bridge resin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/111,677 US4264489A (en) 1980-01-14 1980-01-14 Provisional crown-and-bridge resin containing tetrahydrofuryl methacrylate
US111677 1980-01-14

Publications (1)

Publication Number Publication Date
WO1981002022A1 true WO1981002022A1 (en) 1981-07-23

Family

ID=22339858

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1981/000030 WO1981002022A1 (en) 1980-01-14 1981-01-02 Provisional crown-and-bridge resin

Country Status (8)

Country Link
US (1) US4264489A (enrdf_load_html_response)
EP (1) EP0032249B2 (enrdf_load_html_response)
JP (1) JPH0261492B2 (enrdf_load_html_response)
AT (1) ATE6735T1 (enrdf_load_html_response)
BR (1) BR8105861A (enrdf_load_html_response)
CA (1) CA1134532A (enrdf_load_html_response)
DE (1) DE3067228D1 (enrdf_load_html_response)
WO (1) WO1981002022A1 (enrdf_load_html_response)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2261672A (en) * 1991-11-18 1993-05-26 Michael Braden The use of biomaterials for tissue repair
US5718924A (en) * 1995-01-19 1998-02-17 Eastman Dental Institute Fluoride releasing biomaterials
WO2001050974A1 (en) 2000-01-14 2001-07-19 Denfotex Ltd. Polymerisable resin compositions for use in dentistry
WO2007007065A3 (en) * 2005-07-08 2007-06-07 Depuy Int Ltd Bone cement composition

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088845A3 (en) * 1981-10-12 1985-03-27 Btg International Limited Low shrinkage polymers and process for their preparation
US4511700A (en) * 1982-06-21 1985-04-16 The General Tire & Rubber Company Flexible thermoplastic vinyl chloride polymers
US4500658A (en) * 1983-06-06 1985-02-19 Austenal International, Inc. Radiopaque acrylic resin
FR2686885A1 (fr) * 1992-02-05 1993-08-06 Apsa Resines vinylesters constituees d'un ou plusieurs monomeres acryliques et d'au moins une macromolecule compatible et copolymerisable, et leurs utilisations.
US5367002A (en) * 1992-02-06 1994-11-22 Dentsply Research & Development Corp. Dental composition and method
DE4211040A1 (de) * 1992-04-03 1993-10-07 Muehlbauer Ernst Kg Automatisch anmischbares Mittel zur Anfertigung von Kronen und Brücken
US5965635A (en) * 1995-06-07 1999-10-12 Illinois Tool Works Inc. Alkylacrylate ester composition for anchoring materials in or to concrete or masonry
US5643994A (en) * 1994-09-21 1997-07-01 Illinois Tool Works Inc. Anchoring systems and methods utilizing acrylate compositions
JPH08277207A (ja) * 1995-04-05 1996-10-22 G C:Kk 歯科レジン複合材料用接着剤
ATE221363T1 (de) * 1997-01-13 2002-08-15 Davis Schottlander & Davis Ltd Polymerisierbare zementzusammensetzungen
US5977199A (en) * 1998-02-17 1999-11-02 The Kerr Corporation Composition, delivery system therefor, and method for making temporary crowns and bridges
AU769459C (en) 1999-03-16 2004-07-22 Zms, Llc Precision integral articles
DE19916131A1 (de) * 1999-04-09 2000-10-26 S & C Polymer Silicon & Compos Adhesivsystem für Silicone
US6416690B1 (en) 2000-02-16 2002-07-09 Zms, Llc Precision composite lens
US6846892B2 (en) * 2002-03-11 2005-01-25 Johnson & Johnson Vision Care, Inc. Low polydispersity poly-HEMA compositions
US20060100408A1 (en) * 2002-03-11 2006-05-11 Powell P M Method for forming contact lenses comprising therapeutic agents
US20080041520A1 (en) * 2006-08-18 2008-02-21 Dentsply Research And Development Corp. Adhesive and method for binding artificial plastic teeth
GB201412263D0 (en) * 2014-07-10 2014-08-27 Lucite Internat Speciality Polymers And Resins Ltd A multi-part acrylic cold-curing composition
CN111875748B (zh) * 2020-08-14 2022-10-25 上海沪亮生物医药科技有限公司 一种x光显影临时冠桥树脂及其制备方法
CN113717330B (zh) * 2021-08-26 2023-05-05 爱迪特（秦皇岛）科技股份有限公司 一种光热固化的树脂组合物及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3265768A (en) * 1962-11-19 1966-08-09 Monsanto Co Copolymer mixtures of tetrahydrofurfuryl methacrylate
US3468977A (en) * 1965-10-05 1969-09-23 Bayer Ag Artificial denture compositions and their production
US4001939A (en) * 1967-08-19 1977-01-11 Kulzer & Co. Gmbh Tooth-filling material based on synthetic plastics material

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2877208A (en) * 1956-06-08 1959-03-10 H D Justi & Son Inc Acrylate monomers and polymers of tetrahydropyran methyl alcohol
FR1473474A (fr) * 1966-03-11 1967-03-17 Williams Gold Refining Co Procédé de fabrication de prothèses dentaires en matière synthétique
GB1115544A (en) * 1966-03-14 1968-05-29 Williams Gold Refining Co Method of producing artificial tooth parts from synthetic material
DE2403211C3 (de) * 1974-01-23 1981-12-24 Etablissement Dentaire Ivoclar, Schaan Werkstoff für Dentalzwecke
DE2462271A1 (de) * 1974-01-23 1976-09-09 Dentaire Ivoclar Ets Dentale formkoerper

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3265768A (en) * 1962-11-19 1966-08-09 Monsanto Co Copolymer mixtures of tetrahydrofurfuryl methacrylate
US3468977A (en) * 1965-10-05 1969-09-23 Bayer Ag Artificial denture compositions and their production
US4001939A (en) * 1967-08-19 1977-01-11 Kulzer & Co. Gmbh Tooth-filling material based on synthetic plastics material

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
REINHARDT, "IMPROVING THE ONLAY TEMPORARY RESTORATION" DENTAL STUDENT, VOLUME 57, NO. 4, JANUARY 1979, PAGES 54-55 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2261672A (en) * 1991-11-18 1993-05-26 Michael Braden The use of biomaterials for tissue repair
US5718924A (en) * 1995-01-19 1998-02-17 Eastman Dental Institute Fluoride releasing biomaterials
WO2001050974A1 (en) 2000-01-14 2001-07-19 Denfotex Ltd. Polymerisable resin compositions for use in dentistry
WO2007007065A3 (en) * 2005-07-08 2007-06-07 Depuy Int Ltd Bone cement composition
CN101217986A (zh) * 2005-07-08 2008-07-09 德普伊国际有限公司 骨粘固剂组合物
AU2006268058B2 (en) * 2005-07-08 2012-02-02 Depuy International Limited Bone cement composition
CN101217986B (zh) * 2005-07-08 2014-02-12 德普伊国际有限公司 骨粘固剂组合物

Also Published As

Publication number Publication date
ATE6735T1 (de) 1984-04-15
BR8105861A (pt) 1981-11-17
EP0032249B1 (en) 1984-03-21
JPS56501880A (enrdf_load_html_response) 1981-12-24
EP0032249B2 (en) 1989-06-14
EP0032249A3 (en) 1982-04-14
CA1134532A (en) 1982-10-26
DE3067228D1 (en) 1984-04-26
JPH0261492B2 (enrdf_load_html_response) 1990-12-20
EP0032249A2 (en) 1981-07-22
US4264489A (en) 1981-04-28

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